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Named reactions

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Search synthesis

Morphine

Chemical structure of Morphine
C17H19NO3
Author Gilbert Stork
Publication year 2009
Synthesis type Formal synthesis
Number of steps 22 (linear)
Reference

Browse hundreds of other total syntheses.

Part 1 of 1
Chemical structure
HO(CH2)3OH, TsOH
Dean-Stark
PhMe
Reflux, 85%
Chemical structure
Methyl propynoate, Et3N
THF
-20 to 0 °C, 3.5 h, 89%

See the Michael Addition
Chemical structure
Pd(OAc)2, Ph3P, NaOAc, n-Bu4N+ Cl-
DMF, H2O
125 °C, 4 h, 84%

See the Heck Coupling
Chemical structure
HCl
THF, H2O
0 °C, 90 min, 80%
Chemical structure
Ph3P+CH2OMe Cl-, TMS2NK
THF, CH2Cl2
-30 °C to RT, 15.5 h, 95%

See the Wittig Reaction
Chemical structure
HCl
THF, H2O
RT, 2.5 h, 86%
Chemical structure + Chemical structure
  1. Cp2ZrHCl, AgOTf
  2. TESCl, Imidazole
CH2Cl2
-78 °C to RT, 19.5 h, 95%
Chemical structure
Et3N
Decalin
235-240 °C, 24 h, 55%

See the Diels-Alder Reaction
The yield was 70 % brsm. Also isolated was the C2-epimer (14 % yield).
Chemical structure
LiBHEt3
CH2Cl2
0 °C, 90 min, 86%

The yield was 90 % brsm.
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C to RT, 3.5 h

See the Dess-Martin Oxidation
Chemical structure
Ph3P+CH2OMe Cl-, TMS2NK
THF, CH2Cl2
-50 °C to RT, 15 h, 74% (2 steps)

See the Wittig Reaction
Chemical structure
n-Bu4N+ F-
THF
-50 °C to RT, 2 h, 88%
Chemical structure
Dess-Martin Periodinane
CH2Cl2
0 °C, 4.5 h, 90%

See the Dess-Martin Oxidation
Chemical structure
Li(s-Bu)3BH
THF
-20 °C to RT, 6 h, 53%

The yield was 70 % brsm.
Chemical structure
MsCl, Et3N
CH2Cl2
0 °C, 6 h, 74%

The yield was 90 % brsm.
Chemical structure
HCl
THF, H2O
0 °C, 5 h, 86%

The yield was 98 % brsm.
Chemical structure
MeNH2.HCl, Et3N, NaBH4, Ti(Oi-Pr)4
MeOH
0 °C to RT, 4 h, 93%
Chemical structure
K2CO3
PhH
75 °C, 24 h, 73%
Chemical structure
ClCO2Me, NaHCO3
CHCl3
Reflux, 17 h, 91%
Chemical structure
SeO2, t-BuOOH
H2O
Reflux, 15 h, 72%

The yield was 89 % brsm.
Chemical structure
LiAlH4
Et2O
-30 °C to Reflux, 3.5 h, 82%
Chemical structure

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91% (1 step)

See : J. Med. Chem. 1977, 20, 164.
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